


Someone I Once Was

by WinchesterPartyOfTwo



Category: Supernatural
Genre: Alternate Universe, Amnesia, Cancer, Dean used to be an ass, Eventual Romance, Eventual Smut, Lawyer Dean Winchester, M/M, Protective Dean Winchester, Protective Gabriel, Secretary Castiel, Shy Castiel, Sick Castiel, Slow Burn, corporate Dean
Language: English
Status: In-Progress
Published: 2017-05-22
Updated: 2018-01-26
Packaged: 2018-11-03 18:21:26
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 8
Words: 19,507
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10972806
Author URL: https://archiveofourown.org/users/WinchesterPartyOfTwo/pseuds/WinchesterPartyOfTwo
Summary: Dean Winchester wakes up from a car accident. Besides a concussion, he feels fine. He quickly notices that who he is now, was not who he was before the accident. Instead of cold and uncaring, he is happy, and caring towards others, especially his secretary, Castiel Novak. However, Castiel is battling demons of his own, and may just need Dean to help him overcome this battle.





	1. Chapter 1

**Author's Note:**

> Disclaimer: I do not own Supernatural, or any of the characters. I also have no extensive knowledge of the medical field, or about law offices. 
> 
> All mistakes are mine. 
> 
> Enjoy!

Dean blinked as his eyes adjusted to the bright light around him. It smelled clean, too clean. His mind was foggy. Where was he?

“Thank God you are awake!” a familiar voice said.

His brother Sam’s blurry face soon came into focus. He looked both concerned and frightened.

“Hey Sammy” Dean managed to mumble out. “Where the hell am I?”

“At the hospital….do you not remember what happened?”

Dean gave him a blank stare.

“You were in a car accident. Some guy decided it was a great idea to drink his body weight in alcohol and then drive home. You were hit pretty hard. Concussion, broken ribs, nasty gash to your head and arm. Twenty-eight stiches later, here you are.” Sam gave him another once over. “Do you remember now?”

Dean closed his eyes. The last thing he remembers was working late. He had to get his report out ASAP, and was forced to do an almost all nighter. Once It got to be 3:30am, he called it quits to get some sleep.

Suddenly, he remembered bright lights, a sickening crash, and sirens in the distance.

“Yeah, I think I can piece together what happened.” Dean ran his hand over his forehead. His head was wrapped in gauze, and he felt the beginning of a major headache start up.

Just then, there was a knock at the door. A tall, middle aged doctor made her way to the bed.

“Mr. Winchester, I am glad to see that you are awake. You gave us a little scare. My name is Dr. Mills.” The woman said.

“Uh…Hi.” Dean couldn’t find the energy to say anything more.

“How are you feeling?” Dr. Mills asked “Any nausea, headache, pain in your back or limbs?”

“I can feel a massive headache coming on, but other than that I feel ok. How long have I been out for?”

“Two days. You do have a pretty serious concussion, so that is most likely the cause of your headache. I will go ahead and order you some more pain meds. Do you remember what happened?”

“Umm, I remember working late, then on my way home I got hit by some bright lights, a loud crash, and then it’s pretty much lights out.” Dean was really hoping for some of those pain meds, his head felt like a balloon ready to burst.

“That is normal” Dr. Mills said “Like I said, you hit your head pretty hard. You may experience some memory loss, change in personality, frequent headaches. But nothing too out of the ordinary. I am going to have you stay the night tonight, and then you should be able to head on home tomorrow. I would suggest taking it easy these next few days. From what your brother had told me, you can be a bit of a workaholic.” She gave him a small smirk. “If you can pull yourself away from the office for a few days, do it. If not, then please take it easy. I will make sure the nurse leaves my contact information in your discharge papers. If you notice anything out of the ordinary, or have any questions, please do not hesitate to call me.”

Dr. Mills gave him a warm smile, and said she would be back in a couple of minutes with his pain medication.

Sam thanked her, and she left without another word.

Dean laid back, and covered his eyes with his hand. “Man, I might just have to take her up on that suggestion of taking a few days off. I feel like I could pass out at any moment.”

Sam stared at him like he had just grown two heads. Not hearing a response, Dean removed one of his hands to glance at Sam.

“What?” He sat up a little more in his bed “What’s wrong Sammy?”

Sam shook his head. “You’re serious? YOU are going to take some time off work? Mr. Bad Ass Boss, I need to stay in the office as much as possible, not have a life, and take it out on others?”

Dean stared at him. “Well, if the doctor thinks I should take some time off, I think I should. At least a day. Hell, we both work at the same place, you can always check to make sure things are going a-ok!”

Dean was referring to the law office that he and Sam owned. Winchester & Winchester was their baby that they worked their asses off to open. Dean and Sam were both partners of the firm. There were several associates the worked beneath them, as well as many paralegals and their own secretaries.

Sam was confused. This sounded like a completely different Dean. The Dean he knew was a testy man, always at the office. Yelling orders to his team, running his secretary to the ground, and complaining nonstop. That Dean would never consider taking a minute off work.

He brushed it off for now. Dr. Mills did say that there could be temporary memory loss/personality change. Maybe this was just that.

Dean soon dosed off, and Sam left, telling the nurse to let him know when to be by to pick up Dean. His Impala was at Bobby’s getting fixed, so Dean would need a ride.

…

Two days later, Dean found himself in his apartment. He decided he was going to head back to work tomorrow, so he was sifting through his massive email inbox. Most were from his secretary, informing him of meetings with clients, phone conferences, and a few reports that he has asked him to write up. He answered as many as he could before taking a break.

As he was making himself lunch, he looked around, his apartment looked bland. He thought to himself that he should redecorate a bit.

In the midst of his daydream, his phone rang. He looked at the name on the screen and answered immediately.

“Hey Castiel, what can I do for you?” he said to his secretary.

“Uhh, hi Mr. Winchester…umm, I-I’m so sorry for interrupting you while you are recovering. S-Sam mentioned that you are going to be back tomorrow, and I normally would not have bothered you, but I-I…”

“Cas, get to the point, what’s up man? Something wrong with the Hernandez case? I just read the report, it looked great.”

Cas hesitated a moment. “Um, no. I-I was just wondering if I would be able to come in a little late tomorrow? I had to reschedule my doctor’s appointment, and the only time they had open was tomorrow morning at ten. I can be at the office by noon! I am so, so sorry. I can stay late every day this week, I will do more reports for you, whatever, I am so sorry!”

Dean held his phone away from his ear, wincing at the increase in volume. “Whoa, Cas, don’t worry about it. It is not a big deal at all. I will see you at noon, and if you need to come in later, just shoot me a text.”

“Really?” Castiel sounded shocked.

“Yeah, take your time man. Listen, I have to get back to my mountain of emails, I will see you tomorrow, ok?”

“Y-Yes Mr. Winchester. Thank you so much.”

“Not a problem”

With that, Dean hung up and went back to his laptop. He had to get his things ready for work tomorrow.

…

Castiel sat staring at his phone. Had that really just happened?

“Well, what did he say?” Castiel’s brother, Gabriel asked.

“H-He said it was ok, and if I needed to come in even later, then that was ok as well.” Castiel was stunned. That was not his boss he just got done talking to. His boss would have yelled at him, told him how a good employee would not need to call in, told him he needed to work extra hours…he would have not liked him calling in late.

“Well, then I guess you didn’t need me after all!” Gabriel said. Castiel had asked him to stop by while he called Dean, incase Dean did not allow him to come in late. Gabriel knew how important this appointment was to him, and he was not afraid to stand up to the eldest Winchester.

Gabriel worked at Winchester and Winchester as well. He was a paralegal, but he mostly worked with Sam. The few times he worked with Dean, there had been loud fights, and punches were almost thrown. Gabriel and Dean butted heads constantly; he was not afraid to tell Dean how he felt. That is why Castiel asked him to stop by.

“Yeah, I guess you didn’t need to.” Castiel was still staring at his phone.

“Well bro, I gotta go. Please, please let me know how the appointment goes tomorrow. Oh, and you still owe me that caramel macchiato, for stopping by! Extra sweet, extra whipped cream, and tell them to not skimp on that delicious caramel drizzle!” With that, Gabriel was gone, exiting out of Castiel’s apartment.

Castiel watched him exit, and then put his phone down. What was going on with his boss? I guess he will see tomorrow.

He went to prep his bag for work, it was going to be a long day tomorrow.


	2. Chapter 2

**Notes for the Chapter:**

> Disclaimer: I do not own Supernatural, or any of the characters. I also have no extensive knowledge of the medical field, or about law offices. 
> 
> All mistakes are mine. 
> 
> Constructive criticism is always appreciated, Enjoy!

Castiel looked down at his hands that were on his lap, he was speechless. 

 

"Mr. Novak, please don't fret, we are not sure what we are dealing with yet. We will do a biopsy, and I will let you know where we go from there." His doctor said. 

 

Castiel looked up and nodded. "Ok, I understand." 

 

His doctor stood up and clamped a hand on Castiels shoulder. "It will all work out Castiel. I will walk you down to the room the procedure is done in. I advise you to rest today, if you must go to work, no strenuous activity. The results should be back in a week." 

 

"Thank you Dr. Milton."

 

...

 

 

Dean rode in his Impala on his way to work. He was so glad that Bobby was able to get his Baby fixed up in such a short amount of time. She looked perfect. No one would've known she was in an accident.

 

He pulled into his office building and rolled up his car window. Grabbing his briefcase and cup of coffee, he walked toward the entrance.

 

Walking through the doors, he nodded and waved at the security guard. He pressed the up button on the elevator and waited. Once the elevator dinged, the door opened, and a red headed lady stepped off.

 

“Good morning Charlie.” Dean said.

 

“Oh, um, Hi Mr. Winchester. Good morning! I am, um, just going to get my briefcase from my car. I forgot it. But, don’t worry, I will have that report to you asap!”

 

Dean scrunched his eyebrows together. “Don’t worry about it, take you time. Go grab a coffee while you are at it, it sounds like you need one!” With that, he stepped onto the elevator, leaving a confused looking Charlie walking away.

 

“Hold the elevator!!” a voice screeched.

Dean looked up from his phone quickly, and put his arm out to stop the doors from closing.

Gabriel Novak stepped into the elevator.

“Well, well, I will have to say, I am surprised that you actually cared enough to hold the elevator. Last time we were in this position you pressed down the “door close” button in my face. Did you get laid last night? You are usually a little nicer after you have gotten some.”

He hit the number for the 7th floor.

Dean looked at him. “I woul-“

“Save it Winchester, I don’t want to hear it” Gabriel looked up at Dean, the height difference obviously not bothering him “I will say this though. Thank you for finding the one caring speck of bone in your body, and not giving Cas a hard time about coming in late today. I am glad you did not give him trouble, because I would have beat you down. Cassie doesn’t need your shit, especially now. I don’t know why he even still works for you, but he does. Just leave him alone.”

The elevator dinged, and they both stepped out.

“Gabriel, I have no idea what you are talking about. Cas has worked for me over 5 years. I have no reason to cause him any grief.”

“Yeah, yeah, yeah, like the time he called in sick while puking his guts out, and you told him he would have to work overtime for the next two weeks? Or what about when his car broke down? You sat yelling at him on the phone until the tow truck came, and then continued when he got here. Just let him be. He is going through enough without you being a huge bag of dicks.” With that, Gabriel turned towards the left and went to his cubicle.

Dean stood there for a few moments, then turned to the right to go his office. He went to unlock the door and found a few sticky notes stuck to it. He pulled them off and walked inside. Setting his briefcase on his desk, he sat down and logged into his computer. While it was loading, he read over the sticky notes. One was from Sam, reminding him that they have a meeting at 10. One was from Cas, saying that he sent the last of the requested reports over to him, and once again apologizing for being late today. The rest were simply welcome back/get well messages from coworkers.

His computer loaded, and he went straight to his emails. He spent a few minutes browsing through them, before his office messenger popped up. It was from Sam.

_Sam W: Hey! Welcome back! I am sure you were dying to get back into the office._

_Dean W: Eh, it is nice to get back into the routine._

_Sam W: I bet! Did you get my message about the meeting at 10? It should not be long. Just going over some preliminaries._

_Dean W: Yeah, I got it. Sounds good_

_Sam W: Ok, great! I will stop by around 9:45. We can get some coffee before it starts._

_Dean W: Ok._

_Dean W: Oh, and by the way, do you know what is up Gabriel’s ass today? I got chewed out in the elevator for nothing. Going on and on about me being a dick to Cas._

_Sam W: I have no idea._

_Sam W: But you are kind of hard on him._

Dean stared at the screen, not knowing what to say next.

_Sam W: Maybe just get him a nice card or something. It is his birthday next Monday. I am sure he would appreciate it. Cas does do a lot for you. Anyways, I gotta go, see you soon._

Before Dean could even process anything, there was a knock at his door. Charlie stood there, now with a briefcase in hand.

“Good morning again. I have the papers that you requested.” She stepped in and handed them over to him.

“Thanks Charlie” Dean took them and glanced at them briefly.

“Did I do them wrong? I knew I should have stayed later to look over them more, I am sorry. Let me see them and I will redo them.”

Dean looked up at her. “Charlie, they look fine. I will go over them more after my meeting at 10. Don’t be so hard on yourself”

“Really? Um, I don’t think I have ever heard you say that.” She looked down at her feet, then back at him. “I am going to go back to my desk now, if you need me to revise anything, just let me know” She then walked out of the door.

Dean was confused. Why did it seem like people were walking in circles around him? When he waved at Benny the security guard this morning, he looked like he was about to faint in shock. Then, when he walked to his office, people were happily chatting amongst each other in their cubicles. When they say him, they scatted away to their desks and started working immediately. Now, this whole this with Charlie.

Not to mention the conversation with Castiel last night, and Gabriel’s words in the elevator.

He was just about to open an email that popped up on the computer screen when Sam walked in.

“Hey, you ready? I know I am here a little earlier than I said, but maybe we can grab a quick breakfast along with our coffee? I am starving”

Dean nodded. He stuffed his notes he would need for the meeting into his briefcase, and followed Sam out, locking the door behind him.

…

“I don’t get it Sammy, I feel like some huge bad guy here. Everyone seems so skittish around me.” Dean took another bite of his omelet.

“Well, Dean. You are kind of a dick. This isn’t the first time I have told you this.” Sam was cutting into his own omelet and taking a bite.

“But, I don’t get it, I don’t even know what I did. People are scared to talk to me, Cas sounded like he was going to hyperventilate on the phone late night, and poor Charlie looked like she was going to faint in my office.” Dean looked confused. “I guess I am just an intimidating person.”

Sam looked at him. “Dean, do you remember anything from before the accident?”

“Well, no shit Sammy, of course I do, it is not like I suffered amnesia or something” Dean rolls his eyes and takes a bite of bacon.

“There is the Dean I know” Sam returned the eye roll. “I know you remember your job, your family, your coworker, that kind of stuff. But do you remember YOU?”

“What kind of question is that? Of course I remember me. I can’t just forget me Sam.”

Sam gave him a look. “No, I mean, your personality. You said that Gabriel was talking about the time you made Cas work two weeks of overtime. Do you remember you doing that? Do you remember the way you talked to people? That kind of stuff”

Dean stared at his food. He really did not remember that stuff. But, how could he forget that? This made no sense.

Sam could tell that Dean did not remember.

“Dean, don’t worry, Dr. Mills said there could be memory loss, or a change is personality. If it is still bothersome to you in a week or two, then we can always have you looked at.”

Dean finished his bacon, and put his napkin on the plate. “Yeah, I guess so. I just don’t get how I could have been such a dick and not know it. Hell, I don’t even have the urge to yell at anyone now, how could I have been doing that just over a week ago?”

“I don’t know Dean, but who knows, maybe this is your chance to be Dr. Jekyll instead of your usual Mr. Hyde” Sam smirked at him.

Dean threw a balled-up napkin at him. “Let’s go, we are going to be late for the meeting”

…

Castiel rushed into the office building, hastily giving a wave to Benny and pushing to up button on the elevator several times. It was a little past noon, but he did not believe Dean when he said he could take more time off that necessary. He just hoped he would not have to do overtime again.

Once he reached the 7th floor, he ran to Gabriel’s desk. He was not there, but he set down his disgustingly sweet caramel macchiato onto the desk. He then ran over to his desk.

He glanced into Dean’s office and saw the door closed and the lights off. Good, he was still in his meeting.

“Well, hello there Cas, what brings you in so late?” Charlie came over and said. She had a big smile on her face. Castiel and Charlie were good friends.

“Doctors appointment” Cas said, logging into his computer.

“Sounds like fun, you didn’t miss too much here, just the boss man acting really odd.” Charlie was digging through the candy bowl Castiel kept on his desk.

Cas looked up suddenly. “Oh no, was he mad? I knew I shouldn’t have taken the morning off, now I am going to be working overtime all week! I should send him another email apologizing, maybe he will take pity on me.” He went to open his email.

“Whoah, Cas, take a chill pill. He was not angry at all…which is the weird part. He was…happy? I don’t know, but he was definitely not himself. He actually gave me a compliment, which I have never seen.” She shrugged. “Maybe this accident had an impact on him, who knows.”

Castiel was uncertain if Charlie was just saying this to make him feel better, or if Dean was actually in a good mood.

“Anyways” Charlie said “Your birthday is next week! That is the important thing. What do you want? Do you want to go out to dinner? That new sushi place just opened, and I am dying for some good sushi.”

“Uh, sure. That sounds good. I have not have good sushi in forever. Let’s go there after work on Monday?” Cas smiled, he liked hanging out with Charlie, she always seemed to put him in a good mood.

“It’s a date! Well, not a date, since you are not a woman, but nevertheless, I will be there! I see the boss man coming, so I am out of here. Talk to you on messenger!” She scurried off to her desk.

Castiel smirked, but then it went away when he say Dean talking with Sam. Dean was laughing at something, then he turned and started to walk to his office.

Cas went to open his mouth to say something, but Dean beat him to it.

“Cas! You are here! Perfect. How was your appointment? I hope all went well.”

Cas stared at him. “Uh, Y-yeah, it went fine. Um, I apologize again if I-“

“Cas, what did I say, it is not a problem, things come up. I have another meeting in an hour. I sent you an email this morning with a task list I want done for the day. If you do not get it done, just let me know. The rest can be finished tomorrow.” Dean smiled and unlocked his office door.

Cas was still staring when Dean sat down at his desk. The ping of his messenger snapped him out of his trance. He looked at the screen.

_Gabriel N: Bro! This macchiato is PERFECTION! Thanks a bunch! How did the appointment go?_

_Castiel N: I am glad you are enjoying your sugar rush. They did a biopsy, I will know the results next week._

_Gabriel N: Well, keep me up to date. If you want me to come with you for the results, let me know, Sam won’t mind me taking a few hours off._

_Castiel N: Must be nice to have a boss like that._

_Gabriel N: How was dickbag? Did he give you any trouble about being late? Be honest with me!_

_Castiel N: Dean was actually ok with it still. He smiled at me. I have no idea what is going on, but it is a nice change._

_Gabriel N: He must have gotten laid. Anyways, got to go. I have a lunch date with that hot chick on the second floor! ;)_

Castiel rolled his eyes and opened up the morning email from Dean. He read over it and started up on the tasks due for today. It was nice to not have any deadlines, even if it may only be for today.


	3. Chapter 3

**Notes for the Chapter:**

> Disclaimer: I do not own Supernatural, or any of the characters. I also have no extensive knowledge of the medical field, or about law offices. 
> 
> All mistakes are mine, constructive criticism is welcome!
> 
> Enjoy!

Monday rolled around, and Castiel was in a great mood. It was his birthday today. He had woken up to a text message from his brother saying that he was going to bring him breakfast at the office, so do not worry about that.

Shortly after that, Charlie texted him confirming their sushi plans for tonight. Today was going to be a great day.

He was just about to step out the door when his neighbor across the hall opened her door. A little boy came sprinting out carrying a colorful handmade card.

“Mr. Novak, Mr. Novak! Happy Birthday!! I made you a card!” The boy screeched.

“Ben, there is no need to scream.” His mother scolded.

“Sorry Mom, I am just so excited!” Ben handed Castiel the card, looking proud of himself.

“Thank you Ben, I love it!” Castiel said. Ben smiled wider. Castiel looked at the woman. “Good morning Lisa.”

“Good morning Castiel, Happy Birthday! I hope we are not bothering you.”

“Oh, no, I am just on my way to work.” He smiled.

“I made that card in art class in school! I accidently used too much glitter.” Ben smirked

“I think it is perfect. Thank you Ben.” Castiel ruffled Ben’s hair.

“Ok Ben, we have to get you to school, and I am sure Mr. Novak has to get to work” Lisa said. They waved goodbye to Castiel as he locked his apartment door.

…

Castiel arrived at his desk to find a huge fruit arrangement waiting for him. It was beautiful, with all different kinds of fruits, as well as chocolate covered strawberries and pineapples. He looked around for a card, but did not see one. He opened up the plastic and sampled one of the strawberries. It was perfect. He lifted up the basket and went to take it to the fridge.

On the way to the fridge he ran into Dean.

“Oh, um Mr. Winchester, Hi. I was just putting this in the fridge, and then I will go and log in.” Castiel stuttered out.

“Relax Cas, what have I said, call me Dean. You do not need to call me Mr. Winchester. Anyway, it’s your birthday! I see you found the fruit basket I left on your desk. Do you like it?” Dean looked uncertain.

Castiel was speechless. In the five years he has worked for Dean Winchester, he has never given him a gift, let alone even remembered when his birthday was. Granted, ever since his accident he has been a different man, but he never expected this.

“I love it, thank you very much” Castiel gave him a smile.

Dean let out a breath “I am glad. I have to get back to my office for a conference call. Happy Birthday Cas.”

Castiel thanked him again and went to place the fruit in the refrigerator.

Back at his desk, he logged in and opened his emails. He did not get a chance to do anything else before a box of delicious smelling food was placed in front of him.

“Happy Birthday Cassie!” Gabriel yelled.

Castiel looked up and smiled at his brother. “Thank you Gabe, this smells delicious!”

“Trust me, it is. I got you your usual. Eggs, over easy, extra bacon, hash browns, and a large coffee. Two creams, three sugars.”

“Thank you again, I really appreciate it.” Gabe winked at him before turning to go towards his desk.

Castiel opened up the box and started to dig in. He was responding to a few of Dean’s clients when Charlie stopped by.

“So, I couldn’t help but see this large fruit arrangement in the fridge. Know anything about that?” She smiled.

“Yes Charlie, it is mine, and yes, you can have some.” He smiled knowingly at her. “Dean gave it to me.”

“Oh really?” She didn’t look as shocked as he thought she would be. “Well, maybe we all really have been graced with a new Dean Winchester. I sure as hell hope so, I don’t think I can take going back to all that drama after the nice week we have had.” She snagged one of Cas’s bacon strips. He looked up to glare at her, but instead his eyes went wide.

“What?” She said around a mouth full of bacon.

“Well, Miss Bradbury, I am glad that you are liking this “new Dean” as everybody seems to call it.” Dean smirked at her when she turned around looking like a deer caught in headlights.

“Oh, Mr. Winchester, uh, I, um, I didn’t mean to-“ Charlie looked speechless for once.

Dean grinned. “Charlie, really, it is ok. I am glad that you find the new work environment pleasurable. I do not want my employees to feel uncomfortable. Oh, and please, call me Dean. This whole “Mr. Winchester” is way too formal.”

“Well, thank you Dean. I, uh, I am going to go back to my desk. See you tonight for dinner Cas!”

Castiel waved at her, then looked expectantly at Dean, who was holding a large stack of papers.

“Well, I hate to do this to you on your birthday, but would you be able to file these reports away for me? The Hernandez case is finally going to be closed. I am writing up the report now.”

“Sure thing Dean.” Castiel grabbed the stack and got to work.

…

“Come on Cas!!” Charlie has been hovering at Cas’s desk for the past 10 minutes. “Our reservation is at 6, we are going to be late!”

“Charlie, it is 5:15, the place is 5 minutes away, we are not going to be late.” Cas was in the middle of sorting papers that needed to be shredded. “I just need to finish this, then shred this stack. It will take 15 minutes tops.”

“Ugh, fine. I am going to go to the ATM across the street. When I get back, I expect you to be ready!”

“Fine, fine.” Cas grabbed his stack and went to the shredders.  When he entered the room, Dean was standing at the printer.

“Fuck you, you ass!” Dean kicked the printer, it was obviously jammed. “Oh, Cas, what’s up, aren’t you done for the night?”

“Yeah, um, I just wanted to finish shredding these papers.”

“Ok, but don’t stay too late, you need to celebrate!” Dean finally got his papers from the printer. “Did you by chance get the Hernandez case report I set on your desk? I need that retyped and revised by ASAP.”

“Yes, I saw it. I will make sure it is done first thing in the morning.” Castiel finished his shredding and looked up at Dean.

“You are the best Cas, thanks!”

Castiel watched Dean’s retreating form. He took a deep breath and went to get his things together. Charlie was going to be back any minute.

He grabbed his phone and saw a voicemail on it. He listened to it quick.

“Hello Castiel, this is Dr. Milton. I am calling to let you know that your results are back. It is important that we meet in person to discuss our findings. I have an open appointment at 5:30pm tomorrow. Please let my receptionist know if this works for you.”

Castiel closed his eyes and ran his hand down his face. This was not what he wanted to hear. He quickly called and confirmed that the time works for him. As he was hanging the phone up, Charlie rounded the corner.

“Castiel Novak, are you ready? It has been 20 minutes, and I want some sushi now!”

“Yes, I am ready.” Castiel put on a smile. He was not going to let that phone call ruin his night.

…

“So, Dean actually remembered your birthday? That is some crazy shit. I didn’t even think he knew my name a week ago.” Charlie was munching away on her California rolls, obviously happy with how they tasted.

“Yeah, uh, I didn’t think he even cared.” Cas said. “It was a pleasant surprise. I hope this Dean stays with us, it makes work much more pleasant. Castiel got the spicy tuna rolls, and they were delicious.

“Well, between you and me, I was listening into Sam talk with Inias. He was saying how Dean could stay like this, all happy and pleasant, or could start to become the monster we know him as. Apparently he hit his noggin pretty hard.”

“Well, either way I have no choice but to stay. The benefits are amazing.”

“Yeah, they definitely are.” Charlie took another bite of sushi.

“So, how are things going with Dorthey?” Cas wanted to change the topic, as much as he liked his bosses new attitude, he really did not want to talk about it.

“Oh my, I do not even know where to start. Things seemed to be going well, but then she stopped texting me. Then she called me last week for a quick hook up. Ever since then I have heard nothing from her.” Charlie sighed. “I am going to call her sometime this week and see where we stand.

“That stinks. Maybe you should go after that girl you met online? She seemed pretty legit.” Cas offered.

“But she did not like Harry Potter, so I lost interest” Charlie sighed. “It’s ok, I am still young, I have plenty of ladies to mingle with!”

Cas laughed and ordered another round of drinks for them.

…

Dean sat on the floor of his bedroom. He was looking through a photo album he had kept. The pictures in it ranged from when he was a baby up until just recently. From what he could see, he looked happy. He was smiling in most of the pictures. One picture caught his eye. It was taken about six months ago. It was of him and Sam. They were both dressed in a suit, standing in front of their office sign. That was the day they took on one of the biggest cases of their career. Sam was smiling bright, Dean however, only had a small smile on his face.

Regardless, he looked happy.

Dean shut the book, he just did not see the person he used to be, the person everyone still sees him as. He wished he could remember that Dean, just so he could vow to never be him again. He hated how people were reluctant to talk to him, how they were scared to make him angry. He let out a big sigh.

The only thing he could do from now on was just continue on as he sees fit, definitely not unhappy, and definitely not a “dick” as Sam puts it.

Feeling a massive headache coming on, Dean goes to take a hot shower and get ready for bed.

…

The next morning Castiel was fretting, he was on the verge of a meltdown. He frantically searched his desk from top to bottom to find the Hernandez case report Dean left on his desk yesterday. He knew he saw it, it was here yesterday. A sinking feeling started as he thinks he knows what happened to it.

Dean is not in the office yet, so he vows to search everywhere before he starts to full on panic. He retraces his steps, going to Gabriel’s desk, Charlie’s desk, the elevator bay, the restrooms, the lunchroom, until finally standing in front of the place he hopes it is not in; the copy/shredder room.

He opens the door and starts looking. There is no way he is going to go through the shredded papers, but maybe he accidently left it in here. He looks on the printer, the copier, on top of all the boxes of paper, and on top of the shredder. No such luck. He is about to give up and look somewhere else when he glances a piece of paper stuck in the shredder. He clicks the button to reverse the shredder and feels his stomach drop. Here, in front of him is what remains of the Hernandez reports cover page. It is shredded halfway, and completely ruined. Cas feels like he is going to cry. If this is the cover page, that means the rest of the report has been shredded into a million microscopic pieces.

It was times like this that Cas wished that Dean did all his editing on the computer. He has worked for Dean for five years, he knows how he works. He first types and outline of what the report should look like. Then, he prints it out and handwrites all the important points he wants to include onto the paper. The papers are usually covered with pen scribbles that has taken Castiel forever to decipher.

After that, Dean hands off the papers to Castiel to type into an official report.

How could he be so stupid! How could he have shredded this report without knowing! Dean is going to kill him. This is it, he is going to be the one who snaps happy, caring Dean out of his trance.

Sulking back to his desk, he began thinking of what he could say to Dean. He glanced at his watch, Dean should be here in about 15 minutes. That will give him time to think up a speech.

But, just his luck, he goes to his desk and sees Dean in his office, laughing historically at something one of the associates was saying.

_At least he is in a good mood._ Castiel thought.

He sat in his chair and logged in, hoping that the guy would stay in Dean’s office for a while. He opened up his messenger and decided to message Gabriel.

_Castiel N: Good morning Gabriel. Are you still coming with me to the doctors after work?_

_Gabriel N: Yes sir! Please try not to worry, whatever it is, we will work through it. How was your birthday? Did you eat your body weight in sushi?_

_Castiel N: Haha, no. Unlike you, I do not consume copious amount of foods anytime I can._

_Gabriel N: Hey! I do not do it all the time! Well, maybe I do go on a sweets binge once a week, but that is not the point!_

_Castiel N: Whatever._

_Castiel N: Dean is going to kill me, I accidently shredded the Hernandez case file._

_Gabriel N: OMG_

_Gabriel N: How did you manage to do that!? Do you need me to come down there while you talk to him?_

_Castiel N: It is a long story, I will tell you later. No, please don’t come down. I need to fight my own battles. Someone is in his office now, so I have some time to practice my speech._

_Gabriel N: If I hear any commotion, I am coming down!_

_Castiel N: I gotta go, the guy is leaving._

 Castiel looks up as the gentleman exits Dean’s office. He smiles at Cas as he heads towards the elevator. Cas takes a deep breath and stands up. He walks as slowly as he can to Dean’s office and knocks on the door frame.

Dean looks up and smiles at him. “Cas! Hey, what’s up?” He takes a sip of his coffee. “How is that case report coming? I just got word that I need it complete by tomorrow morning. I know it is long, so I apologize”

“I-I was just coming to talk about that. You see, I-“

“Is my handwriting that bad? I swear, I need to start editing on my computer. It will save you from having to decipher my chicken scratch.” Dean chuckled and took another sip of coffee.

“No, no, it is not that.” Castiel looked as though he was going to cry. “I-I-I am so sorry, I was looking for the report this morning, a-and I could not find it. I retraced my steps and found the Hernandez reports cover page halfway in the shredder. I m-must have shredded it by accident. I am so, so sorry Dean.” Castiel bit his lip and tried his very best to hold in the tears threatening to escape.

Dean looked at him with an emotionless expression. He set his coffee cup down and faced the window behind him. He was silent for a couple of minutes. Castiel was about to say something when Dean slammed his fist on the window, hard.

“GOD DAMN IT!” Dean screamed.

Castiel jumped back, the tears now falling freely down his face. “D-Dean, I-I will do anything to make this up to you. I-I will work nonstop tonight and tomorrow, I-“ Castiel let out a sob.

Dean turned around from the window. He was furious. “Cas, how could this have happened! You have never done this! I-I can’t believe this. Do you KNOW how LONG it took me to write all my notes?” He just about screamed the last part.

“D-Dean, please. I will do anything. J-Just, please don’t fire me. Please. I n-need this job, I promise this won’t ever happen again. I am so sorry. Just, please, let me know what I can do to help!” Cas was begging Dean, tears streaming steadily down his face.

Dean’s face immediately softened. He looked at Castiel and saw the state he was in. He then glanced up to the windows by his office door. People were looking curiously into the office with a mix of emotions on their faces. He walked around Cas’s shaking form and closed his office door and drew the blinds down.

Once he turned around, he placed a hand on Cas’s shoulder. Cas flinched, but looked up at Dean.

“Listen, Cas, I am sorry. That is not the way I should have reacted. I-I just-“ Dean took a calming breath. “it just took me a long time to compile my thoughts about the case onto my report. It is my fault as well for being so old school with my reports”

Castiel looked at Dean, uncertain if he should say something or not. He felt a tear run down his cheek and went to wipe it off. He was surprised when Dean beat him to it and wiped it away with his thumb. Realizing what he did, he took his hand away and took a step back.

“Anyways, why would you think I would fire you Cas? Everyone makes mistakes. This just happens to be a big one….” Dean ran a hand down his face “We can fix this.” He smiles and sat down at his desk, motioning for Cas to sit in the seat across from him.

“Well, you have threatened to fire me in the past for much less than this, s-so I just figured this would be the time I blew it.” Cas reached for the box of tissues on Dean’s desk and wiped his nose.

Dean looked at him oddly for a few moments. “Well, that was the past. The important thing to focus on now is how to write this beast up. I have the outline on my computer, but unfortunately, not my notes.”

“I really am sorry Dean, whatever you need me to do, just tell me” Cas said

“Well, today is pretty open, so I will try to write up as much as I can here. I may just need to pull all-nighter.” Dean said

“Did you want me to stay late too?” Cas really did not want to, but it was his mistake. “I have an appointment after work, but I can come back afterwards”

“Nah, it is my report, I will take care of it. If I have to work on it tonight, I will just work on it at home.” Dean didn’t say this, but the look that Cas gave him when he yelled at him was enough for Dean to let him off the hook. He never wanted to make anyone that frightened again, and if that meant he had to bust his ass to write his report, then so be it.

“I will give you a call if I need help. In the meantime, could you please run across the street and get me a cup of coffee?” Dean reached into his wallet and pulled out some cash. “Also, get a box of coffee and some donuts too, I am sure everyone here can use a sugar rush.” He winked at Cas. “Bring Charlie to help, I am sure she could use a break from her work”

Cas took the money, dumfounded, and then exited the office. He rounded up Charlie and they were off.

…

“So, you literally shredded his report notes for the biggest case of his career, and he basically let you off the hook? He raised his voice and then actually apologized?” Charlie look shocked as she grabbed the two boxes of donuts from the cashier. “THEN he sends you to get coffee and donuts for the office? I swear, I do not know this man. He has never gotten food for the office, let alone acknowledge us.”

“I don’t know Charlie, but I am not going to question it.” Cas grabbed the huge box of coffee, as well as Dean’s normal coffee order. “I am just glad I still have a job”

They headed back to the office, where they were greeted with many surprised faces when they announced who bought them the breakfast treats.

…

Many exhausting hours later, Gabriel and Castiel sit in the doctor’s office waiting for Dr. Milton to come in the room. Castiel had been on edge all day with the whole shredding incident, that he almost forgot about his appointment. When Gabriel came to get him, all the worry came back in an instant.

“Hey, Cas, please take a breath.” Gabriel put a hand on Cas’s knee. “We don’t even know the results yet.”

No sooner had he said that did Dr. Milton knock on the door and enter the room.

“Good evening Castiel, Mr. Novak.” He said to them. He sat down in his chair and took a deep breath. “As you know, the cat scan that you had a couple weeks ago showed a mass on your brain. We now have the results of the biopsy to see if it is cancerous or not.”

“Yes, I know. What are the results.” Cas just needed an answer. The constant headaches, dizziness, loss of balance, mild confusion. All of these symptoms he tried to brush away as stress until Gabriel dragged him to be looked at by a doctor. Now, here they were.

“Castiel, the results show that you have stage 2 brain cancer.” Dr. Milton said “The good news, is that it does not seems to be spreading aggressively. There is a great chance that we can treat this.”

Cas had no idea what to say. He has cancer? No, this can’t be right, there is no way that these headaches are cancer.

“Headaches are the most common symptom of brain tumors.” When Cas looked up, he realized that he must have said what he was thinking aloud.

Gabriel spoke up, realizing that Cas needed to process what he has been told. “What treatment are we talking about Doc? Chemotherapy? Surgery?”

“Chemotherapy is the most effective. The tumor is in a place where surgery would be dangerous. However, if the chemo does not show signs of improvement, we may need to take that route.”

Castiel sat there in a haze as his brother and doctor talked about his treatment options.

**Notes for the Chapter:**

> I know this chapter was mainly Castiel focused, but don’t worry, we will be getting to Dean next chapter!


	4. Chapter 4

**Notes for the Chapter:**

> I am so sorry for the delay, things have been so crazy! Here is another chapter, I hope you all like it, I will try to post again real soon!
> 
> Disclaimer: I do not own Supernatural, or any of the characters. I also have no extensive knowledge of the medical field, or about law offices. 
> 
> All mistakes are mine, constructive criticism is welcome!

...

_“Are you fucking KIDDING ME?!” Dean shouted at Castiel from across his desk. “I told you that I needed those copies on my desk by this morning, what is your excuse now?”_

_“W-well Mr. Winchester, I did-did not get the email that you sent, I-“ Cas stuttered_

_“Bullshit, this is ridiculous. Those copies better be on my desk in the next five minutes or you are fired.” Dean slammed his hand on his desk and Cas ran out the door._

_Dean went to his computer and started to type up an email. Exactly 4 minutes later, Castiel came in looking frazzled._

_“H-here are the copies. I-I apologize, t-this won’t happen again.” Cas put the stack of papers on the desk._

_“It better not. Now go start up on your daily tasks before I change my mind about firing you.” Dean replied coolly without looking up from his computer screen._

_Cas looked like he was about to say something. Dean looked up._

_“I said GO!” Dean shouted_

Dean shot up from bed suddenly, startled.

He closed his eyes and took a deep breath. _Damn, that has been the third dream I have had like that._ He could feel a headache trying to rear its ugly face.

He got up from bed and moved his laptop and notes aside. He has finished most of the report, but still have a few things to touch up. He goes into the kitchen to make himself a cup of coffee. As the pot is brewing, he goes to get some pain meds for his headache. He then glances at the time.

3:28am

At this point, there was no point in going back to bed. He should just stay up and finish the report. Maybe he can fit in a good run before he has to go into the office.

He pours his coffee and leans against the counter as he takes a sip. _Was that man really me?_ Of all the flashbacks he has had of him before the accident, that one was the most upsetting. The way he yelled at Cas, how he barely looked him in the eyes, and the most upsetting, the look of fear on Castiel’s face.

He shook the thoughts from his head, _that was the old me._

As he drank the rest of his coffee, he walked around his apartment. It was very bare, just the necessities. Couch, recliner, television, that kind of stuff. Very few decorations, no pictures on the walls. In fact, the only picture that was on display in the whole apartment was a framed picture of him and Sammy on his nightstand.

It was as though his apartment was a showcase, the things inside only to be seen, not touched. Nothing out of place. It was eerie, and Dean wanted to change it. He wanted to look forward to coming home after a long day at the office. Be able to kick his shoes off, crack open a beer, and prop his feet up on the Lazy Boy while watching the game.

He drained the last of the coffee and went back to his laptop on the bed. He turned on some music and went back to typing.

Four hours, three cups of coffee, and one very long run later, Dean had finished the report and was unlocking his office door. Not many people were here yet, as they were not required to be at work until 9. Dean liked the silence. He went about checking his emails, ready for the day to start.

…

Castiel sat in his car outside of Winchester & Winchester. He still felt numb after the news he had gotten yesterday at the doctors. After the appointment, Gabriel drove him home and they talked about the appointment. Castiel had chosen to go through with chemotherapy, and see how his body reacted to it. Dr. Milton referred him to an oncologist, Dr. Barnes, who he said he trusted immensely.

His first round of chemo was on Friday, and he would be going weekly. Gabriel said he would take him to his appointments, and stay with him over the weekends if needed.

Now, all Cas needed to do was act as normal as he could at work. Gabe insisted that he tell Dean, maybe he will lighten his work load. Cas assured him that he would be ok. Besides, Dean has already lightened his work duties a lot after the accident.

He got out of this car and entered the building.

When he go to his desk, he was surprised to see that Dean had his door open. It was 8:30, so it was still rater early. He put his stuff down and went to knock on Dean’s door.

“Um…Hi Dean. Good Morning.” He cautious said, not wanting to interrupt him after the fiasco yesterday.  

To his pleasant surprise, Dean looked up smiling.

“Hey Cas! You are here early, everything ok?”

“Yeah, I just couldn’t sleep, so I decided to come in, maybe you needed help with that case report? I really do apologize, that will not happen again” Cas said

“Hey, things happen, at least there was enough time to fix it. I actually pulled almost an all nighter and got it done! Would you mind looking over it to make sure there are no mistakes? I need to turn it in at 9 sharp!” Dean handed him over the report.

“Yes, of course Dean, I will do it right away.” Cas grabbed the report and went to sit back at his desk.

…

Cas sighed, it was good to be home.

The rest of the day was a very long day. Gabriel kept an annoying close distance to him, practically not leaving him out of sight. Then Charlie kept pestering him about his appointment, begging to know what happened. Cas assured her that he would tell her after work.

Last of all, Dean seemed to be alright with having to pull an all nightery for Cas’ mistake. He was not complaining, but it was still odd. Usually Cas would feel like he would need to apologize one hundred times to make up for it.

But, no. Dean just smiled at him when we left for the day, thanking Cas for his work, and telling him to have a good night.

Cas just brushed it aside. Charlie was going to be here any minute, and he needed to be prepared. Cas knew that Charlie would react similarly to Gabe; sympathetic and overprotective. He went to order their favorite take out, and waited for her to come bursting through the door.

…

Friday morning came, and Dean had a lot on his plate. He was meeting with a client in two hours and he had no idea where his notes were. He swore that he put them in his file cabinet, but there were nowhere to be found. Cas was not going to be back at work until Monday, and he was freaking out.

He glanced at his watch and decided that if he could not find them in 20 minutes, he would call Cas quick.

Meanwhile, Castiel was sitting at his doctor’s office Friday morning. He was exhausted already and he had not even had his treatment yet. He was hoping to get this over with quickly, but knew that was not going to happen.

He sighed and put his head in his hands. He had a massive migraine that was pounding relentlessly. He had not gotten much sleep because of it, and he was secretly glad that Gabriel convinced him to take the whole day off of work. He could not wait to be home in his nice warm bed.

Speaking of Gabriel, he plopped into the chair next to Cas and offered him a water and a bagel.

“Thank Gabe, but I really have no appitite.” Cas grabbed the water, but left the bagel.

“Suit yourself bro, but you need as much energy as you can.” Gabriel but the bagel back into the bag, and started munching on his donut and coffee.

Cas was glad that Gabriel did not go any further into his lecture. He knew things were about to get a lot worse, but he did not want to think about that now. He was already still trying to process everything going on, and having Gabriel (and most likely Charlie) pestering him, was not going to help.

He was just about to take a sit of water when his phone rang.

“Hello?”

“Cas! Thank God you answered!” an extremely frazzled Dean said “I am so sorry to bother you on your day off, but I have NO idea where the notes for my meeting today are. Do you by chance know?”

Cas blinked, his mind fuzzy. He remembered printing them off for Dean yesterday.

“Have you checked your file cabinet? I assumed that I put them there?”

“Yes! I checked there, and I checked my desk, the printer, my personal printer, under my desk, EVERYWHERE!” Dean started pacing his office.

“Um, I really have not idea Dean, I-“

“Castiel Novak” a nurse called

“Shit, Dean, I really need to go, I know I printed them off, just look around. I am so sorry.” Cas hung up the phone and stood up, as did Gabe.

“Do you want me to come with you?” Gabe looked worried.

“Yes, that would be really great”

…

Dean stared at his phone. Cas never hung up on him, let alone left him hanging in a moment of crisis. He knew this was his day off, but damn.

He sighed and decided to look around again. He went to go to the printer room to look, when something caught his eye on Cas’ desk.

There, sitting on the middle of Cas’ desk, were the notes he was looking for.

This made no sense.

Cas knew that those notes held personal information on them, and needed to be in a locked office when someone was not around. This meant that these notes were laying on his desk since yesterday.

Cas was very good at his job, this was so unlike him.

Dean took the notes, and praised the Lord that he found them. He hoped that the people he had working in his office were trustworthy, and the notes went untouched.

He would question Castiel about it on Monday.

Dean went to lock his office, and then made his way to the elevators.

As he was waiting for the elevator, he heard someone join him.

“Good Morning Mr. Winchester” a bubbly voice said.

“Charlie, what did I say? Please, call me Dean.” Dean smirked at her.

“Sorry, old habit” she said as the doors opened.

“Well, that is the past, this is the present” Dean said as he walked into the elevator. Charlie smiled and went to type something into her tablet.

Dean looked at her, hesitated, and the said “Hey, is everything alright with Cas?”

Her head snapped up “W-Why would you ask me that?”

“He has just been acting a little distant, and he just seems a little off”

Charlie looked concerned “Well, I know he has just been under some stress lately, but other than that, who knows, he is a tough cookie!”  

“Well, today I found out that he-“ Dean stopped himself. He did not want to go telling other employees about the little mix up that Cas did without talking about it with Cas himself. “Never mind, like you said, he is a tough cookie.”

The way that Charlie looked at him make him think that there was more to this whole Cas situation than she would let on.

The elevator door opened, and they got out.

“You know Cas, he is a private person, but if he has a concern I know he will speak up” Charlie said “Plus, now that you are not all mean and aggressive, we are all more prone to share our concerns”

Dean grinned “And what concerns are those?”

“Maybe the fact that tomorrow is my birthday and you didn’t get me any fancy fruit arrangement?”

“Well, maybe if you were my secretary I would have” Dean laughed and made a mental note to pick up a little something for Charlie on Monday.

She grinned, gave him a wink, and walked away.

…

It was Friday night and Cas felt horrible. He thanked Gabe tremendously for helping him home after his chemo, but assured him that he was just going to sleep the rest of the day. He wasn’t exactly wrong about that. He looked at the clock and it was 8pm. He has slept for almost 9 hours, and he would have slept for more if it were not for the wave of nausea that rolled over him.

So, now he was on his cold bathroom floor, hugging the porcelain throne.

His doctor has told him that he would feel this way, but Cas did not think it would come on this fast.

As Cas was heaving once again into his toilet, he wished he would have took Gabe up on his offer to stay the weekend.

He wished he had someone here.


	5. Chapter 5

**Notes for the Chapter:**

> So, so sorry for this long delay! We have been going through a bit of a crisis, and are just starting to recover a bit. I am planning to be updating weekly now, and maybe even twice a week if I can get the chapters out!
> 
> Thank you so much for your patience!
> 
> …
> 
> Disclaimer: I do not own Supernatural, or any of the characters. I also have no extensive knowledge of the medical field, or about law offices.
> 
> All mistakes are mine, constructive criticism is welcome!

 

Castiel looked at his alarm clock. The blaring light read 6:30 am. He had been up since 2:00 am. He just could not relax enough to fall asleep.

He finally just decided to get up, his alarm would be going off soon anyways. As he sat up in bed, a wave of nausea hit him. It has been about a month since his first chemo treatment, and he has had two more since then.

He has another today…yay. Usually he had them on Fridays, but this week he had to go on Thursday.

Nausea has been no stranger to him, so he tries to just brush it off. Once he eats something, he should feel better. Plus, he has basically bought out all the ginger ale in the city, so he should be set.

Cas gets out of bed, and starts to get ready for the day. Shower, shave, brush teeth, and breakfast. He is sitting waiting for his coffee to brew when he gets a text from Gabe.

_Hey Bro! I don’t know if I am going to be able to talk to you much before your treatment today, but I just want to say that you will be completely fine!  Charlie is picking you up right? I am so sorry that I am not able to make it, you know I would be there if I could. Please, please let me know when you are home and safe. Love you Cas._

Cas smiled, his brother did have a soft spot for him. Gabe was currently with Sam across the state on a business matter. He would not be back until Sunday morning.

_Gabe, you do not have to worry about me. Enjoy your meetings, I will call you tonight. Yes, Charlie is going with me. Love you too._

He hit the send button and went to drink his coffee. What he had failed to tell him was that Charlie was going to some comic convention this weekend, so she was not going to be able to stay with his tonight and tomorrow, the worst days.

What he also failed to tell him was that he was planning on going to work tomorrow.

Cas knew that Gabe would kill him if he knew that, but Cas could not afford to blow all his PTO. Call him a workaholic, but ever since Dean has been the “new him”, work has not been too bad. He has plenty of time off, but Cas wanted to save it.

He drained his cup and grabbed his briefcase. He could take on today.

…

Cas was filing through some papers on his desk when Dean came over.

“Hey Cas, how are you doing today?”

Castiel looked up to see Dean standing there with a large coffee and some delicious looking pastries.

“Well, I am a lot better now that you are here! Is that for me?” Cas pointed at the coffee.

“As a matter of fact, it is!” Dean gave Cas the coffee and dug out a chocolate pastry, “I, uh, also made sure to get you your favorite, chocolate.”

If Cas didn’t know any better, he would think that Dean was acting…shy? He has a light blush on his cheeks that is adorable.

_Adorable?_ Cas thought. Before he could say anything, Charlie came over.

“We still on for this afternoon?” She asked Cas “Ohhh! Pastries!” She grabbed one from Dean and turned to Cas.

“Yes, we are” Cas said after a sip of coffee.

“Perfect!” Charlie said though a mouthful of pastry.

“Well, as much as I love watching you guys eat, I have a meeting to get to. Cas, are you still able to come with me to that meeting we have offsite tomorrow? This client has a big case, and I will definitely need you to take notes.” Dean said

“Yeah, I can” Cas smiled

“Thank you, I will see you later. Enjoy the sweets!” Dean said and winked at Cas.

“Oh, I will!” Cas grinned and was about to take another bite of pastry when he caught the look on Charlies face.

“Ok, I am going to let that whole wink and little flirty thing you guys had going on there go, but that is just because I am going to yell at you for working tomorrow. What the hell! You do not need to come in!  You have a billion hours of PTO, and you are having CHEMO tonight!” Charlie whispered the last part harshly “Dean can take his own damn notes tomorrow.”

“Charlie, I will be fine, I don’t want to use PTO. I will be fine, usually I don’t start feeling bad until the night after the treatment” That was a lie, bit Cas was not going to tell her that.

Charlie looked at him intently. “I think you just want to spend time with Dean”

Cas blushed and took a sip of coffee.

“That’s it!!! You have a crush on Dean! I knew I didn’t mistake those googly eyes you guys have going on.”

“Charlie, that is not the case, I just don’t want to lose out on my vacation time.” Cas tried to convince himself that was the reason, but he could not deny that he had started to get butterflies in his stomach lately whenever Dean was around.

…

“So, when are you going to tell Dean?”

Charlie was currently driving him to the hospital.

“I don’t know, I don’t think I will need to” Cas was avoiding looking at her and stared out the window.

“What do you mean you won’t need too? I know you are a private person, but this is something you should communicate with your boss. What if the chemo makes you lose your hair? You need to say something. Or what if you are not well enough to do your work and need to take extended time off? Or what if you end up needing that surgery?” Charlie looked concerned “I know you don’t want to think about the negatives Cas, but this is important.”

Cas stayed quiet. He did not want to be treated differently, and he knew if he told Dean, he would be. That, combines with company gossip…he could not handle that.

“Please, just tell me that you will think about it, ok?” Charlie pleaded.

“I go back to Dr. Milton in 3 weeks for a follow up. I will decide then. That is when we will know if the chemo is working or not.”

Charlie looked skeptical, but let it go.

…  

“Are you absolutely sure you do not need me to stay? I can easily head to the convention tomorrow morning.” Charlie said as she was helping Castiel sit on his couch.

“I am fine, go! You have been waiting forever to go to this.” Cas assured “I am just going to sleep for the rest of the day, you would be bored anyways.”

“Cas, you are as pale as a ghost, are you always like this afterwards?”

No, usually it took a day or so to feel the effects, but Charlie did not need to know that.

“Yes, now go!” Cas put on his best smile, and it must have assured Charlie because she kissed him on the cheek and grabbed her bag.

“I have a casserole in the fridge if you are hungry. Don’t forget to call Gabe!” She said as she closed the door.

Cas laid back on the couch and sighed. He grabbed his phone off the coffee table and called Gabe.

…

Across town, Dean was fretting. He was meeting with a big client tomorrow, and he wanted to look his best. He shuffled through his suits, trying to see which one would be best.

_Well, I could go with the black suit with the green shirt. It would match my eyes. Or I could go with the gray suit and the blue shirt. That way it would match Cas’ eyes…_

_Wait, what?_

Dean shook his head. He had been thinking about his blue-eyed secretary a lot lately. He did not know if it was because they had been very busy these last few weeks, or if it was something more. He could not deny that those baby blues could make his stomach flip.

Dean grabbed the gray suit with blue shirt and hung it outside the closet.

…

The next day Cas found himself feeling horrible.

He had been up all night throwing up, and had only just managed to get a few hours of sleep. He went to make some coffee, but as soon as he smelt it brewing, he raced to the bathroom.

This was going to be a long day.

As he raced into the office to get his things together, he stopped suddenly at the elevator. Maybe he should have just stayed home. He pressed the button to go up and leaned against the wall.

“Hey Cas!”

Castiel’s eyes snapped open to see Dean staring at him.

“Hello Dean” He said as the elevator opened.

“You ready to head out soon? I just need to type out an email quick and then I will be ready. You want me to drive?”

Cas felt a little relieved “Yes, that would be great if you could drive.” The elevator dinged and they both got out.

“Perfect. Will you be ready in 15 minutes?”

“Yes, I will be.”

“Ok, see you then!” Dean walked over to his office and unlocked the door.

Cas went to his desk and sat down. While his computer was booting up, he put his head on his desk. He did not feel like being here at all. Maybe Dean will let him leave after this meeting. He browsed through his emails while waiting for Dean.

“Ready Cas?” Dean walked over. “You alright? You don’t look too hot.”

“Yeah, I am fine. Just tired.” Cas stood up slowly and walked with Dean.

“So, I actually just got off the phone with the client. This meeting should not be too long. He is just really concerned about finding a lawyer that will represent him well. Apparently the last one he had was not good at all.”

“Sounds good” That was the best news Cas could hear.

…

Exactly 2 hours and 46 minutes later, not that Cas was counting, they were done with the meeting. Cas had been queasy the whole meeting, and was waiting as patiently as he could for Dean to be done talking. They both shook the clients hand and started to leave.

“Well, that went really well. Thank you so much Cas for coming. It helped so much to have you there so I could concentrate on the client…”  Dean kept talking, but Cas was not listening. He was going to be sick.

Like, now.

He was searching frantically for a restroom, when he found one across the hall.

“Be right back!” Cas stammered and ran inside. He thanked the Lord that it was only a single restroom, and just barely made it to the toilet in time to puke.

Dean watched Cas run to the bathroom. He was confused until he heard the loud retching coming from it. He gave Cas a minute to calm down, then tapped lightly on the door.

“Uh, Cas? You ok in there?”

Cas sat on the cold floor and sighed. “Y-Yes, j-just give me a minute.”

“Ok”

Cas stood up and went over to the sink. He splashed some water on his face and swished some around in his mouth. He looked up in the mirror. He looked horrible. He was pale as a sheet, had big bags under his eyes, and was shaking slightly.

He knew he could not stay in here forever, so he opened the door to go and face Dean.

“Cas? Are you alright? You look like you are going to pass out any second. Here, sit down here.” Dean lead him over to a bench in the hallway. Cas sat down and looked up at Dean.

“I am fine, I just think I need to go home.”

“Yes, yes, of course! Here, lets go to the car and I will take you back to the office.”

They walked out to the car and Dean opened the door for Cas and helped him in. Dean got in on the drivers side and observed Cas leaning against the passenger door.

“Cas? How about I just take you home. I can have one of the guys at the office bring your car back, or maybe Gabriel or Sam can when they get back Sunday.”

At this point Cas could not think straight, so he just hummed in response.

“I’ll take that as a yes.” Dean said as he put the car in drive.


	6. Chapter 6

**Notes for the Chapter:**

> Disclaimer: I do not own Supernatural, or any of the characters. I also have no extensive knowledge of the medical field, or about law offices.   
> As per usual, all mistakes are mine, constructive criticism always welcome!

Cas woke up to the smell of something delicious. He was lying on his couch in his apartment. He had no idea how he got here, or how long he had been asleep. He ran a hand through his hair and sat up. When he sat up he noticed the puke bucket sitting on the floor.

He groaned and decided to follow the delicious smell into his kitchen.

He would deal with that later.

To his surprise, Dean Winchester was standing at his stove, stirring something. He heard Cas at the doorway and turned towards him.

“Hey, how are you feeling? I am making some soup for you if you are up to it.”

Cas was confused. “Why are you in my kitchen?”

Dean smiled. “Well, you fell asleep on the way here, so when we got here I woke you up to come to your apartment. You were barely conscious, so I led you to your couch. I figured you would be asleep for a while, so I went to get some ingredients for my Mom’s famous chicken noodle soup.”

“You didn’t have to do that, I would have been fine” Cas assured.

“Yeah, says the guy who puked his guts out more times in the past 5 hours that I have in my life.”

Cas blushed. He is glad he could not remember much.

“Well, I should be good now if you need to go. You didn’t need to miss work for me.”

“Don’t worry about it, I didn’t have much to do anyways.” Dean said as he scooped some soup in a bowl for him. “And I can’t leave, I am under strict orders from Gabriel to stay with you.”

Cas shot him a look. “You called Gabriel??”

“I know if something happened to Sam while I was out of town, I would want to know.” Dean shrugged “I was on the phone with Sam when I let it slip that I was over here taking care of you. Sam told Gabe, and the rest is history.”

“Yes, but it’s probably just the flu.” Cas tried to convince him.

“Well if it is the flu, then it’s a pretty nasty case” Dean handed Cas the bowl of soup. “They are on their way back home, by the way, their business got done a lot sooner that they expected.” 

Cas groaned and went to go back to the couch to sit down, Dean following behind him.

“When will he be back?” Cas asked.

“In the next hour or so”

Cas knew Gabriel was not happy. He just hoped he would wait until Dean left to lecture him.

“Eat” Dean said, pointing to his soup. “You will feel better, trust me.”

Cas took a bite of soup and moaned. It was delicious.

Dean grinned. “I told you!” He then went and started eating his own bowl.

They sat comfortably eating their soup. When Cas was on his second bowl, Dean broke the silence.

“Can I ask you a question Cas?”

“Sure” Cas put his bowl down on the coffee table.

“You obviously have not been feeling well all day, why didn’t you just call off work?”

Cas stared at his soup. “I thought I could handle it. I knew that you needed me there to take notes.”

“Cas, I am a big boy, I could have taken my own notes. I can’t deny that it was nice to have you there so I could concentrate on the client, but I would have survived.” Dean was looking at him with concern in his eyes. “Just, if you are sick, don’t feel like you need to come to work. Take the time that you need to recover.”

Castiel nodded. “I apologize. I guess I am still stuck in the ways of before.”

Dean stared at him with a blank face. “What do you mean?”

“You know, the whole ‘Call in sick and you are fired’ rule?”

Dean smirked. “I see, the old me?”

“Correct” Cas smiled.

“Well, you can be assured that is not the case anymore. I might have been an ass in the past, but I am not one now. Or, at least I don’t want to be.”

“You have improved quite a bit from the uptight ass you used to be” Cas said as he went to finish his soup.

“Well, thank you. Do you want any more soup? If not, I can go and put the rest in the freezer. That stuff freezes great! You will have soup for weeks.”

“No, I am good. Thank you. You do not need to do that.” Cas went to stand up.

“Hey, sit down. I got this. Sit here, finish your soup, watch some TV! I will take care of the leftovers.” Dean said and went to the kitchen.

Dean rummaged through the cupboards until he found some containers that would work well to freeze. He could not help thinking about what Cas had said. We he really that mean of a boss that he would not even let his employees take a sick day? He mulled over that though while he put the leftovers away and into the freezer.

After they were put away, he leaned against the counter for a bit. He had to know what things were like pre-amnesia. Sam would not go into it, but maybe Cas would.

When he made his way back into the living room, Cas was sitting on the couch cuddled into a blanket. The TV was on with some history documentary playing.

He looked adorable.

Dean went to sit in the recliner and thought about how he was going to start this conversation.

“Hey, uh, Cas? Can I ask you another question?”

“I’m going to have to start charging you.” Cas chuckled “Go ahead.”

“Well, I-I was just thinking. What was I like? You know, before the whole accident and amnesia.”

Cas looked at him for a bit before asking “What do you want to know?”

“Well, you know, what was I like? Obviously, I wasn’t a very nice guy, so, what did I do? What is different about me now that before?”

“Well, for one, you actually talk to your staff now. Before you would barely acknowledge anyone. If we got a ‘Hi’ out of you, that would be a miracle. All communication was done in e-mail for the most part. On the rare occasions that we would have meetings, you would just be there yelling at us, telling us to get out head out of our asses and work harder. Having a conversation with you was unpleasant, so most staff just avoided it.” Cas started picking at his blanket. “Um, let’s see, you definitely did not celebrate colleagues’ birthdays, or get them an extravagant fruit basket.” Castiel smirked at Dean, trying to lighten the mood.

Dean sat there, absorbing everything in. He didn’t have time to think of something to say before Cas continued.

“The one person that you seemed to be halfway pleasant to was your brother. You didn’t seem to be as angry to him. You were probably the hardest on me. Or at least that is what Gabriel always told me. You and he had many of blowouts. It’s a shock that you never fired him on the spot, because you did that a lot. Probably because he is one of Sam’s best workers.”

“What do you mean I was the hardest on you?” Dean asked

“Well, you were always harping on me to get your reports done faster, or to check me emails more often, or that I did not get you the correct coffee. It was petty stuff like that.” Cas avoided eye contact.

Dean looked down at his hands for a bit and then asked quietly. “It I was that much of a dick that I would complain about a damn coffee, why didn’t you just quit? I know that you have a pretty impressive literature degree, why would you stay a secretary for an unhappy lawyer?”

“Honestly Dean? Because I need the money. You pay very well. I could never get a job somewhere else and make the same amount. Yes, I have that degree, and I would love to someday become a writer, or maybe a college professor…but that takes time and money.”

Dean nodded and stood up. “I’ll be back”

Cas watched him go towards the bathroom and almost regretted telling him what he had requested. Yes, Dean was not the more pleasant person pre-amnesia, but he was a completely different man now. Cas couldn’t even imagine him going back to what he used to be.

He stood up as well and went to the kitchen for a glass of water. As he was filling him glass, he glanced at the clock on the stove. If Dean’s calculations were correct, Gabe and Sam should be back soon. As much as he loved his brother, he was not looking forward to seeing him.

He downed his glass of water, and was onto his second one when he heard Dean approach the kitchen. When Cas looks at him, he could see that Dean was visibly distraught. He had red rimmed eyes and a deep frown on his face.

“Are you all right Dean?”

“I should be the one asking you that.”

“We both know that I am starting to feel better, but you are looking worse. What happened?”

“I don’t know Cas.” Dean sighed “Just, having you say all of those things makes me feel like I was a monster. I have so much love for life now, and I love my work and colleges. I can’t believe I was that mean to them, especially you!” He ran a hand through his hair and stepped closer to Cas.

“Cas, you are one hell of a secretary. Even though you are so overqualified for this job, you give it your all! I can’t imagine that you have changed the way you work from before, so that means that I was yelling at you for doing a good job. That makes me sick! If I was doing that to you, that means that I was doing it to others too.” Dean whispered the last part, almost as if he was realizing it for the first time.

Cas closed the distance between then and put a hand on Dean’s shoulder.

“Dean, yes, you were not a great person before, but look at you now. You said it yourself, you love your work and the people you work with. Who knows what you did or what happened during that crash to grant you this second chance at a happy life, but savor it. Take advantage of it! Take risks that you never thought of doing before, actually use some vacation and get away from the office. You know that you have a competent team.” Cas looked him in the eyes “You are not a bitter, unhappy person now. Stop concentrating on the past. You are a young, successful lawyer.”

Dean looked into Cas’s eyes, getting lost in them. _Take risks, Cas said it himself._ And with that though, he closed the space between them and kissed Cas softly on the lips. The kiss started off soft, but quickly deepened. Soon, Cas was pinned against his fridge, both men putting all they had into the kiss.

They did not hear the door to the apartment open, or their two brothers walking in. It wasn’t until they heard Gabe clear his throat that they separated.

“Well, when I said to stay here to take care of my brother, this is not exactly what I meant.” Gabe said with a slight smirk.

“Uh…I wasn’t, w-we weren’t…” Dean stuttered.

“Gabe, this isn’t what it looks like.” Cas said

“So, you are Dean were not kissing in your kitchen? Because that’s sure what it looks like.”

“Gabe, please.” Cas pleaded.

Gabriel and Cas stared at each other for a moment, almost having a silent conversation.

“Fine” Gabe huffed. “Thank you, Dean, for making sure that Cas got home safe, and for taking care of him. I can take over from here, even though it looks like he is feeling MUCH better now.” He wiggled his eyebrows suggestively.

“No problem, I, uh, I will see you on Monday Cas. Um, let me know if you need anything, ok?” Dean said.

“I will, thank you Dean.” Cas looked at him, unsure what to do.

Dean went to grab his bag and just before him and Sam left, he turned to Cas “Call me sometime this weekend, you know, when you are feeling better.” He shot him a smile and then left with Sam.

After the door closed, Cas purposely avoided looking at Gabe until he reached the couch. Gabe followed him in and sat next to him.

After the silence became too much, Cas finally broke and said “Well, just get it over with, yell at me like I know you want to.”

“You know what Cas, I do want to yell at you so bad for being a dumbass and going to work the day after you had chemo. I want to yell at you for pushing yourself when you know that is the last thing you should be doing. But, for some reason, I think you know all of this already. I don’t think you need me to lecture you.” Gabe said “However, what I do what to know, is why you were kissing your boss in your kitchen?”

Cas sighed, he would rather take the lecture.

 


	7. Chapter 7

**Notes for the Chapter:**

> Disclaimer is the same as previous chapters 
> 
> As per usual, all mistakes are mine, constructive criticism is always welcome!

Castiel was uncertain on how to answer Gabriel’s question. He couldn’t deny that he wanted the kiss to happen, but he didn’t really know what lead up to it.

“I don’t know Gabe. I guess the whole situation is a bit of a blur. I mean, I woke up from everything that happened, and Dean Winchester is standing in the kitchen making me soup. Delicious soup I may add. Then, we got to talking. We talked about how we was, you know, before the accident. He seemed genuinely upset about the things I was saying.” Castiel was pacing in his living room while Gabe was sitting on the recliner. “He then went to the bathroom. I went to get a glass of water, and then when he came out, things happened…”

“Things happened?” Gabe repeated.

Cas rolled his eyes and plopped down onto the couch. “Well, you know, we kissed.”

“So, that is all, you kissed? Who initiated it?”

“I don’t know Gabe, I think it was Dean, but it could have been mutual”

“So, you are saying that you wanted to kiss Dean?” Gabe was almost grinning, but still trying to keep a serious face.

Cas stayed quiet while looking down at the floor.

“Wait, I was just joking, are you saying that you really did want to kiss him?” Gabriel was sitting up straight.

Cas remained silent.

“Castiel! Is this something that has been brewing for a while? Or were you just swept off your feet by him because he drove you home and cooked you soup?” Gabe was almost off the chair by this point. “Are you going to answer me? Because this is something that we need to talk about! Do you not remember how much of a dick this guy was to you? All the stupid things he made you do for him? Those ridiculous errands he made you run for no reason?”

“Yes, Gabe, I do.” Cas finally said. “He is not any of those things now, he is one of the nicest, most down to Earth person I know. Yeah, he used to be an ass, but he is not now”

“Don’t you think he could go back to being that? This ‘amnesia’ could wear off at any time. What are you going to do then?”

“I don’t know-“

“Or, if you are actually going to go through with this relationship, how is it going to affect your work? You are his secretary!”

“Gabe, there is not a relations-“

“OR, maybe the most important question of them ALL…when are you going to tell him about your cancer? If you decide on a relationship or not, he needs to know. Look what happened today.”

“You think I don’t know that!” Cas snapped.

Gabriel shut his mouth and waited.

Castiel sighed, he felt a massive migraine coming on. “I’m sorry Gabe. It’s just, there is not a relationship yet. It was just a kiss. There is no need to get all worked up about it.”

Gabe stood up and sat down next to Castiel.

“Cas, believe it or not, but you two do have a relationship. You have a working one. It may not be romantic, but you do have one. As a boss, it’s not fair for you to keep this to yourself. What if it starts to affect your work more? And if you guys do decide to explore a more romantic relationship, it is only fair to not keep secrets. I know you hate talking about this kind of stuff, and I know that you especially don’t like talking about your tumor, but I am just looking out for you. You’re my only family, I love you”

Cas started to tear up. “I know Gabe, it’s just…I might have something good happen with Dean. I don’t want to blow it by saying I have cancer right off the bat.”

Gabe wrapped his arms around him. “I know Cas, and I’m sorry I upset you. I’m just looking out for you. I know it is your decision who to tell, I just don’t want to see you hurt.”

Cas nodded into Gabe’s shoulder.

Across town, Sam and Dean were have a similar conversation.

“So, you and Cas?” Sam said to Dean as they sat in his living room.

“Shut is Sam, I don’t even know what will come of this.”

“Well, who initiated the kiss?”

“I, uh, I think it was me.”

“You think?” Sam was giving him a look.

“I don’t know Sammy, it all happened kind of fast.”

“Well, what are you guys going to do now?” Sam asked as he took a swig of beer.

Dean was looking down at his own bottle of beer and shrugged. “I really don’t know. I mean, I really like Cas. He is smart, kind, compassionate, and apparently really knows how to put up with all my BS.” Dean smirked. “But, I don’t know if he wants to same. We had a pretty good talk before everything happened. I asked him to tell me a little bit about how I was pre-amnesia. The stuff he said was crazy Sammy, like me not letting people call in sick for work, and yelling constantly at Cas. I just don’t see why Cas would be interested in me, even if I am different now.”

Sam started at him for a bit, then finished the rest of his beer.

“You know what Dean? You were an ass, we all know that, but are you a mean spiteful dick now?” He asked.

“I don’t think I am.”

“That’s right, you’re not. Do you have your moments? Yes, we all do, but you are not nearly the person you were before. Why are you not embracing this and letting yourself be happy?”

“I don’t know Sam, just drop it.”

“No Dean, I will not. You have always been a go-getter, pre-and post amnesia. If you want something, you pursue it, you don’t make excuses. If you want this relationship with Cas, why are you so hesitant?”

Dean stared at him for a second and said, “I’m scared.”

“Scared of what?”

“I am scared that this whole amnesia thing will go away and I will end up being this horrible person I was before! I am scared that if I go and pursue this with Cas, I might fuck things up. I am scared to do anything because at any given moment I may wake up and be the huge asshole again that everyone hated and avoided.” Dean looked at Sam and said in a softer voice, “I just want to wait and see what happens. Like I said before, it was only one kiss. It might not even mean anything.”

Sam nodded his head. “I’m sorry for pushing you Dean, I just want to see you happy, and I think being with Cas can do that. Cas is a great guy. Just, trust your gut with this one, ok?”

Dean nodded and forced a smile. “I will Sammy.”

…

It was now Sunday and Dean was out in town running some errands. He desperately needed to buy groceries, but he decided to save that for last. For now, he was picking out some new décor for the cave that he called home. He loved his apartment, but he needed some kind of decorations to make it a real home.

As he was walking up and down the aisles, he decided on a few picture frames, some throw pillows, and a few miscellaneous decorations and wall hangings.

Dean smiled down at his purchases, content with his findings.

He was just about to go towards the checkout when something caught his eye.

“Well, what do we have here?” He said excitedly as he found a lamp made from different parts of vintage cars. It was a beauty. He was contemplating how he was going to fit it in his cart when his phone started to ring.

He glanced at the caller ID and answered immediately.

“Hi Cas! How are you?”

“Hello Dean, I am doing well, how are you?”

“Good, good, just out running some errands.”

The line was silent for a few seconds while each tried to figure out what to say.

“Um, you told me to call you when I was feeling better. I-uh, I am feeling a lot better now. I wanted to thank you again for what you did on Friday.”

“Hey Cas, it’s not a problem. You would have done the same for me.” Dean laughed a bit. “I couldn’t leave you at the client site like that, and I certainly was not going to let you drive home.”

Cas chuckled, “I know, I just wanted to thank you again.”

“You are very welcome.” Dean went and put the lamp in his cart. “Do you think you are going to be ok to be at work tomorrow?”

“Yes, I should be. I have been relaxing all weekend, or should I say Gabriel has been forcing me to relax. If I feel sick I will call you.”

“I am glad Gabe made you law low, you were looking pretty pale. The good thing is whatever flu bug you caught has not made it into the office…well not yet. Hopefully I didn’t jinx it!”

_If only you knew._ “No, it looks like the office is clear from my sickness.”

They fell into an awkward silence, both not knowing how to address the elephant in the room.

Dean chose to break the silence. “Well, I am very glad that you are feeling better Cas, and if you need anything, please don’t hesitate to ask.” He then started to walk towards the checkout lane.

“I will. Thank you again. I will, uh, see you tomorrow.” Cas said.

“Sounds good Cas!”

They both held on the line for a few seconds, then Cas replied, “Goodbye Dean.”

…

Monday came by in full force. Cas and Dean fell back into their usual routine, both avoiding the obvious fact that they shared a pretty heated kiss a few nights prior.

Cas was reading though Dean’s emails and making his weekly appointments when he got a message from Charlie.

_Charlie B: Well, I would say Happy Monday, but you have some explaining to do mister!_

_Castiel N: Please Charlie, I know I messed up, just drop it, please._

_Charlie B: I warned you Castiel!_

_Charlie B: But fine, I will let it drop._

_Charlie B: From what Gabriel told me, you have already learned your lesson._

Castiel stilled from what he was doing. Did Gabriel tell her what happened with Dean? Surely he would know that was something he did not want spread around the company grapevine.

_Castiel N: Really? What else did he tell you?_

_Charlie B: Just that you were being a brat all weekend and did not want to relax. Are you feeling better now? Because no one would blame you for leaving early._

_Castiel N: I’m feeling much better, still a little wear, but nothing compared to Friday._

_Charlie B: I heard from a little birdie that a certain boss of ours drove you home….is that true?_

Castiel rolled his eyes and typed back;

_Castiel N: Yes, he did, he was very nice about the whole situation._

_Charlie B: I WANT DETAILS!_

_Castiel N: There isn’t any details to share. He drove me home, that is all._

_Charlie B: I don’t care, I want to know all about it. When are your free for dinner?_

_Castiel N: Let’s do Thursday._

_Charlie B: I am holding you to it Novak!_

Castiel grinned, this was going to be an interesting week.

 

**Notes for the Chapter:**

> Thank you all who have reviewed and left kudos, it makes my day!! 
> 
> If you are interested in more chapters, please let me know!


	8. Chapter 8

**Notes for the Chapter:**

> Here is another chapter! I apologize for the delay, I hope you like it! 
> 
> Disclaimer is the same as previous chapters   
> As per usual, all mistakes are mine, constructive criticism always welcome!

About a week and a half had passed since “the kiss”, and nothing had really changed between Dean and Cas.

There was still the prolonged eye contact.

The “accidental” touching of the hands.

Dean bringing Cas coffee every morning.

But, other than that, things stayed pretty normal.

Until one Friday morning.

Cas was filing away some old cases when Charlie came up to him.

“Well, hey sunshine! How are you today? You haven’t been at your computer like, all day. How am I supposed to make it though Friday without gossiping with you!”

“There isn’t any gossip to talk about” Cas said without looking up from the folder he was looking at.

“Come on, there has to be something. Dean working on anything juicy that you can spill some details?”

“Dean doesn’t have any cases now, hence why I am glued to the filing cabinets today.”

“Ugh, Castiel! This is not helping my Friday at all! It’s only noon, we still have four hours to go!” Charlie threw her hands up in the air dramatically.

Before Cas could come up with a response, he heard a familiar voice say. “Well, you could always try working to pass the day along.”  He looked up from his filling to see Dean standing behind Charlie.

Charlie whipped around and stuttered out a response. “W-well, I was working, I-uh, I was just seeing what Cas was up to, you know.” She turned a bright shade of red and looked down.

“Relax Charlie, I’m joking. I know it’s slow today.” Dean laughed and leaned against the filing cabinets.

She smiled, but her cheeks remained pink.

“So, I was actually about to kick Cas away from all this filing and take a break, how about you join him? Go get yourselves some lunch”

“I’m down for that!” Charlie perked up. “Let me grab my stuff, meet me at the elevators!”

Dean stared at her retreating form. “Well, she didn’t need any encouragement” He turned to Cas. “You, however, do.” He closed the file Cas was holding and shit the cabinets door.

“Hey! I was in the middle-“

“Cas, go take a break. You have been doing this for hours, not to mention you did this all of yesterday. It really isn’t that important”

Cas huffed and looked up at Dean.

Dean stared back. He opened his mouth like he was about to say something, but the closed it.

“I, um, I am going to go get ready for lunch I guess.” Cas went to walk past Dean.

“Wait, Cas.” Dean put his hand on his shoulder.

Castiel turned around to look at Dean again.

“I was thinking. Would you, uh, want to go get dinner sometime this weekend?”

Cas looked at him stunned.

“You don’t have to, I was just thinking it would be nice to get together after work. I would really like to-“

“Yes, that sounds nice” Cas said smiling.

“Really? Man, I for sure thought you were going to say no”

“Well, I would be a fool to. Is this a…date? Or just casual coworkers?”

Dean stared at him for a second. “Do you want it to be a date?”

Before Cas could respond, a fiery red head bounded around the corner. “Castiel! Let’s go! It is not often that Dean lets up go for an extended lunch, let’s go before he changed his mind!” She grabbed his forearm and pulled his to the elevators. “Bye Dean, thanks again!” she called over her shoulder.

Dean smirked and walked to his office.

…

Cas and Charlie just finished ordering their lunch and were going to find a table. Once they were settled in, Cas smirked at his friend and said, “I may have some gossip for you.”

“Really? Spill!” She said while putting some sugar in her lemonade.

“Dean may have just asked me out on a date.”

“No way! About time! You too have had the googly eyes for each other for a while now.”

“I don’t even know if it is a date or not.”

“What do you mean you don’t know?”

“Well, we didn’t really get to finish the conversation before you came barging over.” He smirked.

“Don’t go blaming this on me, you know how I get when it comes to food.”

“He asked me to go to dinner this weekend, I said yes, then asked if it was a date. He asked me if I wanted it to be a date, and that is when you came over.”

“Sounds like he wants it to be a date.” She smiled “If he didn’t, he would’ve just said no”

“Yeah, I guess.”

Charlie could tell that he was not interested in talking more about this topic.

“So, when do you go back to your doctor to see how the chemo is doing?”

Cas glared across the table, obviously not wanting to talk about that either.

“Come on Cas, I’m just worried about you.”

Cas sighed. “I go back in two weeks, I was supposed to go there today, but he had to reschedule. I have chemo next Friday though.”

He thankfully did not have to go into detail when the waiter that came over with their food.

…

Dean was sitting at his desk later that day, organizing his notes so he could come back to them on Monday. He just got off the phone with a potential new client, so he wanted to make sure everything was good to go for next week.

He picked up his phone to make a call when there was a knock on the door. He looked up to see Cas standing there.

“Hey Cas, come on in” He motioned to the empty chair across from him.

Cas came over to his desk but remained standing.

“Yes.”

“What?” Dean asked, confused.

“Yes. I want dinner this weekend to be a date.”

Dean grinned and stood up, he was about to hug Cas when he realized where they were. Instead, he went to lean on the desk next to him.

“So, when do you want to go? Does Saturday sound good? Where do you want to go?”

Cas smiled. “Pick me up at 6 tomorrow. I’ll let you pick the place.”

“Sounds good. I’ll let you know when I am on my way.”

“I’ll look forward to it.” He did a quick glance out of Dean’s office windows. The office was dead, mostly everyone had left to go home already. He turned back and moved closer to Dean. Cas leaned in and pressed his lip softly to Deans. The kiss lasted only a few seconds before Cas backed away and smirked at Dean. “I’ll see you tomorrow” He said as he walked out the door.

Dean watches him leave, speechless.

…

Dean woke early Saturday morning, he looked over at his clock and saw that it was only 5:00am. He tossed and turned for the next half hour and then decided to just get up. He dragged himself into his kitchen and started his coffee maker. As he waited for his coffee to brew he contemplated going for a run. One glance at his phone told him that was not happening, it was currently 20 degrees outside. He didn’t mind running in the cold, but he was not feeling up to it today.

He went into his office and sat at his desk. While sipping his coffee, he looked at his planner. His day was pretty much open. Since it had been so quiet at work this week, he has been able to get a lot of stuff done at work.

This left more time to get ready for his date with Castiel.

Date.

That was a word that was new to Dean. He hadn’t dated someone in years; always so consumed by his work.

He already knew where he was going to take him. There was this Italian place downtown that he loved, and he hoped Cas loved it too. He overheard him talking to Charlie one day about his love for pasta.

Plus, he was good friends with the head chef there, so he knew the food would be fantastic.

He logged into his computer to start some work when his phone dinged. He glanced at it and saw it was a text from Cas.

**_From: Castiel Novak_ **

**_Good morning, I can’t wait for tonight. Do I need to dress up?_ **

Dean smiled, of course Cas would be concerned about being underdressed.

**_To: Castiel Novak_ **

**_Good morning! Just wear a nice shirt and jeans, I can’t wait either. 6pm still work?_ **

Dean went back into his kitchen to wash out his coffee mug. As he went to refill it, his phone alerted him of another message.

**_From: Castiel Novak_ **

**_Yes, 6pm, do you still have my address?_ **

Dean typed out his response.

**_To: Castiel Novak_ **

**_Yup, see you then!_ **

Dean looked at the clock on the stove. He still had hours to kill before he had to start getting ready. He decided to go for a run after all.

…

It was 5:30pm, and Castiel was pacing across his apartment. He knew he shouldn’t be nervous, but he was. He had already had numerous phone calls with both Charlie and Gabriel throughout the day to help his nerves.

Charlie kept telling him to relax, and just be himself. She came over earlier that day to help him pick out his outfit; a pair of dark jeans with a white button-down shirt with a blue vest over it. She told him to let his know ASAP how tonight went.

Gabriel, on the other hand, was leerier about his date. Cas knew that him and Dean never got along, but that was before his accident. Dean used to be a jerk; never admitting his faults and blaming others for his own mistakes. Gabriel would be the first one to call him out and put him in his place. Of course, Dean didn’t like that at all, but since Gabe technically works for Sam, there was nothing he could do.

Gabriel said he was excited for Cas, but just warned him to be careful.

Castiel knew what he was referring to.

He didn’t want to talk about that with Dean, at least not now.

It was their first date, there was no way he was going to bring it down by telling him he has cancer. That is definitely not first date worthy.

Cas knows that Gabe is just looking out for him, they are all they have left after their parents died. Gabe has always been protective of him, and with the current state of things, it has only amplified.

He was lost in his thoughts when he heard a knock on the door. Cas took a deep breath and walked over to reveal Dean standing on the other side. He looked amazing in light jeans and what looked like a plaid shirt underneath his jacket.

“Hey Cas” Dean smiled.

“Hello Dean, come on in, I just need to grab my jacket.” Cas stepped aside and closed the door behind him.

“No rush, our reservations aren’t until 6:30, and I am a little early.”

Cas smirked and grabbed his coat anyway. “So, where are we going?”

“Do you like Italian?” Dean grinned, knowing his answer already.

“I love it!”

“Well, there is this place downtown, Michelangelo’s. They have the best food! Trust me, I know.”

“I haven’t been there, which is surprising. Charlie and I have been to almost every restaurant within a 30-mile radius.” Cas said as he put his jacket on.

“You will love it, I promise. If you don’t, I owe you another date.” Dean said, following Cas to the door.

“Well, let’s hope that you owe me another date regardless.” Cas locked his door and turned to Dean.

“I’m sure that can be arranged.” He put his hand on Cas’s lower back and lead his to his car.

The drive to the restaurant went quickly; Cas’s apartment was close to the downtown area. Once they arrived there, Dean went to open the car door for Cas.

“You are going to love this place.” Dean said, closing the door.

Cas looked up at the building, and then back at Dean. “This looks amazing.”

“It is, trust me. Now let’s go inside, it’s freezing out here.”

Once they were inside and settled into their table, Cas took a better look around. This place was very nice. Like 5 star restaurant nice. There was no way Dean could have gotten a reservation with only a 24 hour notice.  He looked across the table at Dean and rose an eyebrow.

“What?” Dean asked.

“How on Earth did you get us a table at a place like this on a Saturday night? Especially with only a days’ notice!” Cas looked around again, it was definitely a full house.

“Let’s just says I have connections. It’s no big deal.”

“Connections?”

Before Dean could respond, the waitress came over to get their drink orders. Cas decided to drop the topic for now.

“What do you recommend here?” He asked Dean.

“Just about anything is amazing. If you are going for a classic, their Fettuccini Alfredo is great. The veal stuffed tortellini is what I usually get, other than that, their gnocchi is outstanding, as well as their chicken marsala.”

“Chicken marsala, I think I will go for that.”

The waitress returned with their drinks and they placed their order.

“So, Cas, I know you said before that you hope to become a writer, is that something you still want to do?” Dean asked

Cas took a sip of his wine and said “Yeah, one of these days I hope to. Like I said before, it takes time and money, and I really don’t have either right now.” He took another sip “But one day, yes. I think it would be amazing to be able to scratch that off my bucket list.”

“Bucket list? What other things are on there?” Dean asked, intrigued.

“Wouldn’t you like to know. I have to leave something for us to talk about on future dates.” Cas teased.

“Very true.”

“What about you Dean? What would you like to do with your life? You are already a successful lawyer, is they anything else you hope to accomplish?”

“Honestly? I hope to one day open a car restoration shop. I fully restored my Baby from the ground up, and I love it. I find it relaxing.” Dean looked at Cas, gauging his reaction. “I know, it sounds silly.”

“I don’t think it’s silly at all. Having something to keep you mind off all the lawyer stuff is key. Plus, having that shop open I’m sure won’t even feel like a job, more like a hobby.”

“Yeah, that is what I am going for. Don’t get me wrong, I love being a lawyer, but I just don’t see me doing that for the rest of my life.”

“I can respect that.”

“I have never told anybody that, not even Sammy. I guess I am afraid of what people will say, or if they would judge me for eventually leaving a career that I worked hard for.”

“Life is short, you have to do what makes you happy.”

“Yeah, you do.”

Shortly after, their waitress came over with their meals. Dean got the veal stuffed tortellini, and Cas opted for the chicken marsala.

“Oh my God, this is fantastic!” Cas said around his first bite.

“Told ya.” Dean smiled as he started on his plate. They continued to talk throughout the meal. Dean learned that Cas went to college with Charlie, and that is where they became friends. He also learned about Cas’s parents, and why Gabe was so protective of Cas. Dean touched a bit on his family, but didn’t go too much into it, not wanting to ruin the mood of the evening. Once they were done with dinner, a man came over to the table.

“Well, well, well, Dean Winchester. It’s been a while since I have seen you here.”

“Benny! Hey, I was hoping I would be able to see you tonight.” Dean stood up and shook the guys hand. “Cas, this is Benny, he is the head chef here.”

Cas stood up to shake the guys hand. “Head chef? So, this is your ‘connection’?”

Benny laughed and looked at Dean, “I like this guy. Yeah, Dean called me yesterday begging me to get him a table tonight. He’s lucky I love him like a brother, because it wasn’t easy.”

Dean and Cas both sat back down.

“I am glad you were able to get us a table, dinner was fantastic!” Cas told him.

“Great! I was just coming over to see how you liked your food. Did you leave any room for dessert?”

Dean looked at Cas for an answer, and he shook his head.

“I couldn’t eat anymore if I tried.”

Benny laughed and clapped Dean on the shoulder. “Then my work here is done. I got to get back to the kitchen. Don’t be a stranger Dean.” He pointed at Dean and walked away. The waitress came back with their bill, and Dean beat Cas for it.

“I’m packing next time.” Cas argued.

Dean just smirked and handed his card to the waitress.

…

Dean was walking Cas to his apartment when he said, “I had a really great time tonight, I would love to do it again.”

“Me too.”

“How does next Saturday sound?”

Cas hesitated, he had chemo next Friday, he knew he wouldn’t be in any shape to go on a date.

“I, uh. I can’t next week.” Dean’s smile dropped a bit. “But I can do it next Thursday! If you don’t mind doing it during the week.”

Dean’s smile returned. “Thursday works great.”

They stared at each other for a moment before Dean said, “This is the part where I would kiss you for the first time, but since that has already happened, fuck it.” He leaned in and pressed his lips to Castiel’s. Cas responded instantly and wrapped his hands around his neck. Dean backed him up to his apartment door and deepened the kiss, sliding his tongue across his lips. They stayed like that for a few minutes before Dean reluctantly pulled away.

“As much as I am enjoying this, it’s freezing out here, and I don’t want to rush things by going inside.

Cas nodded at him, agreeing.

“I had a great time tonight Cas, I can’t wait for Thursday.”

“Me either.” Cas said. He leaned up to give Dean one more kiss. “See you on Monday.”

“Yeah, see you Cas, have a good night.”

“You too Dean.”

Dean made sure Cas made it inside safely and walked back to his car, a smile plastered to his face.

 

 


End file.
